Sodium hydride → HCID 22414273, compound

HRID 1721279Notes

Reaction equation

HRID 1721279 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O-:15].[Na+].[H-].[Na+]>CO>[Cl:13][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH3:12])=[CH:11][C:2]([O:15][CH3:14])=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1088002,7-Dichloro-4-methylquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 22414273HCID 22414273, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Chloroquinoline 14 (7.0 g; 32.8 mmol) was added to a solution of sodium methoxide in methanol generated from 1.08 g (36.1 mmol) of 80% sodium hydride in 80 ml of methanol. The resulting mixture was refluxed overnight. It was filtered while still hot to remove undissolved matter. The product crystallized from the methanol upon cooling to deliver 6.1 g (70%) of 15 as a white solid. 1H NMR (CDCl3);: δ2.62 (s, 3H); 4.10 (s, 3H); 6.78 (s, 1H); 7.38 (d, 1H); 7.81 (d, 1H); 7.93 (d, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. filtrationIt was filtered while still hot
  3. customto remove undissolved matter
  4. customThe product crystallized from the methanol
  5. temperatureupon cooling

Sources & evidence

ORD record
ord-c1ad68f68b5e4751aaba5d3a8df1a1de
Source dataset
uspto-grants-1996_04
Patent number
US05510338

Reaction notes

Loading…